10,549

Oakland, MD Homes

Section Image
  • /34

    $399,900

    • 2 Beds
    • 1 Bath
    • 887 Sq Ft

    565 Glendale Rd Unit 303B, Oakland, MD 21550

    Experience lakefront living at its finest in the premier unit at Silver Tree Suites! This beautifully updated 2-bedroom, 1-bath condo showcases rustic charm with custom woodworking throughout. Featuring two separate living areas, there's plenty of space to relax and entertain. Enjoy year-round lake views from the private balcony, unwind by either of the two fireplaces, and appreciate the added

    Sean Sober Taylor-Made Deep Creek Real Estate, LLC

    565 Glendale Rd Unit 303B, Oakland, MD 21550
  • /11

    $375,000

    Sold Apr 30, 2026

    2173 King Wildesen Rd, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • Built 2025

    Last Sold Summary

    • 0 Days On Market

    Current Estimated Value $375,281

    Last Listing Agent Betsy Spiker Holcomb Taylor-Made Deep Creek Real Estate, LLC

    2173 King Wildesen Rd, Oakland, MD 21550
    • /21

      Est $264,689

      Not Listed For Sale

      17 Laurel Brook Dr, Oakland, MD 21550

      • 3 Beds
      • 3 Baths
      • 1,840 Sq Ft
      • Built 1991
      17 Laurel Brook Dr, Oakland, MD 21550

      Last Sold Summary

      • 171 Days On Market

      Last Listing Agent Michael Cumerlato Jason Mitchell Group

  • /22

    $159,000

    • Land
    • 2.02 Acres
    • $78,713 per Acre

    22 Woodlands Hill Ln, Oakland, MD 21550

    2.02-acre wooded building lot in The View community at Deep Creek Lake. This beautiful parcel offers a private setting with plenty of room for your future mountain or lake area retreat. Seasonal mountain and lake views. Conveniently located off Lakeshore Drive and just minutes from Deep Creek Lake, Wisp Resort, restaurants, shopping, and other area amenities. Enjoy the perfect combination of

    Jon Bell Railey Realty, Inc.

    22 Woodlands Hill Ln, Oakland, MD 21550
  • /47

    $260,000

    Sold Feb 27, 2026

    20160 Garrett Hwy Unit H708, Oakland, MD 21550

    • 1 Bed
    • 1 Bath
    • 550 Sq Ft
    • Built 1972

    Last Sold Summary

    • $473/SF
    • 234 Days On Market

    Current Estimated Value $269,069

    Last Listing Agent Charlotte Savoy The KW Collective

    20160 Garrett Hwy Unit H708, Oakland, MD 21550
    • /70

      Est $1,648,087

      Not Listed For Sale

      22 Duck Cove Rd, Oakland, MD 21550

      • 4 Beds
      • 3.5 Baths
      • 1,964 Sq Ft
      • Built 1960
      22 Duck Cove Rd, Oakland, MD 21550

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Betsy Spiker Holcomb Taylor-Made Deep Creek Real Estate, LLC

  • /61

    $319,999

    Under Contract
    • 4 Beds
    • 2 Baths
    • 1,416 Sq Ft

    595 Pysell Crosscut Rd, Oakland, MD 21550

    Enjoy peaceful living just outside of Oakland, Maryland, with this 4-bedroom, 2-bath home situated on 2.14 acres. A large open yard with a tree-lined perimeter creates a private setting while still keeping you close to town, shopping, dining, and Deep Creek Lake area activities. The main level features a roomy kitchen with great cabinet space, a butcher block island, and an easy flow into the

    Jay Quinn Taylor-Made Deep Creek Real Estate, LLC

    595 Pysell Crosscut Rd, Oakland, MD 21550
  • /107

    $1,350,000

    Sold Sep 19, 2025

    421 Penn Cove Rd, Oakland, MD 21550

    • 4 Beds
    • 3.5 Baths
    • 4,284 Sq Ft
    • Built 1986

    Last Sold Summary

    • $315/SF
    • 54 Days On Market

    Current Estimated Value $1,540,945

    Last Listing Agent Steven Ritchie Railey Realty, Inc.

    421 Penn Cove Rd, Oakland, MD 21550
    • /41

      Est $338,441

      Not Listed For Sale

      139 Hunters Dr, Oakland, MD 21550

      • 4 Beds
      • 2.5 Baths
      • 2,240 Sq Ft
      • Built 1991
      139 Hunters Dr, Oakland, MD 21550

      Last Sold Summary

      • 45 Days On Market

      Last Listing Agent Nina Beitzel Railey Realty, Inc.

  • /44

    $1,450,000

    • 3 Beds
    • 2 Baths
    • 1,695 Sq Ft

    187 Lower Penn Point Dr, Oakland, MD 21550

    Cozy cottage with split lakefront and Type A dock located in the serene quiet Penn Point Cove. This quaint home has plenty of room for family, guests and entertaining. The covered & heated outdoor deck facing the lake is a great place for morning coffee and evening dinner. The large, bright kitchen & dining area is another great entertaining space with quartz countertops, stainless steel

    Amy Mangum Railey Realty, Inc.

    187 Lower Penn Point Dr, Oakland, MD 21550
  • /100

    $1,860,000

    Sold Oct 06, 2025

    237 Glendale Rd, Oakland, MD 21550

    • 7 Beds
    • 6.5 Baths
    • 3,735 Sq Ft
    • Built 2002

    Last Sold Summary

    • $498/SF
    • 88 Days On Market

    Current Estimated Value $1,975,176

    Last Listing Agent Bill Weissgerber Railey Realty, Inc.

    237 Glendale Rd, Oakland, MD 21550
    • /49

      Est $895,923

      Not Listed For Sale

      158 Silver Tree Ln, Oakland, MD 21550

      • 5 Beds
      • 4.5 Baths
      • 2,250 Sq Ft
      • Built 2003
      158 Silver Tree Ln, Oakland, MD 21550

      Last Sold Summary

      • 79 Days On Market

      Last Listing Agent Jon Bell Railey Realty, Inc.

  • /43

    $179,000

    • 3 Beds
    • 1 Bath
    • 1,516 Sq Ft

    40 Sunshine Ln, Oakland, MD 21550

    Enjoy the charm of country living with the convenience of being in downtown Crellin! Situated on nearly an acre, this inviting 3-bedroom, 1-bath home offers a bright, open layout filled with natural light.The main level features a spacious bedroom surrounded by windows, creating a warm and welcoming retreat. Upstairs, you'll find two additional bedrooms that can easily accommodate family,

    Danielle Luscombe Taylor-Made Deep Creek Real Estate, LLC

    40 Sunshine Ln, Oakland, MD 21550
  • /2

    $699,000

    Sold Jul 31, 2026

    1875 Pysell Crosscut Rd, Oakland, MD 21550

    • 5 Beds
    • 5 Baths
    • 3,664 Sq Ft
    • Built 2004

    Last Sold Summary

    • 5% Below List Price
    • $191/SF
    • 38 Days On Market

    Current Estimated Value $737,877

    Last Listing Agent Dan Shockey Taylor-Made Deep Creek Real Estate, LLC

    1875 Pysell Crosscut Rd, Oakland, MD 21550
    • /83

      Est $2,491,877

      Not Listed For Sale

      320 Lake Forest Dr, Oakland, MD 21550

      • 6 Beds
      • 4.5 Baths
      • 2,363 Sq Ft
      • Built 1997
      320 Lake Forest Dr, Oakland, MD 21550

      Last Sold Summary

      • 111 Days On Market

      Last Listing Agent Lauren McCann Railey Realty, Inc.

  • /49

    $875,000

    Under Contract
    • 4 Beds
    • 3 Baths
    • 2,280 Sq Ft

    37 Skippers Point Rd, Oakland, MD 21550

    4BR/3BA lake access home on Skippers Point WITH dock slip! One-level living in a private setting near the deep waters of Deep Creek dam. Features include an attached, over-sized 2 car garage with 2nd floor storage, whole house generator, electric vehicle charger, stacked stone exterior, mud room. hardwood floors and solid surface countertops throughout kitchen and bathrooms. Enjoy a huge master

    Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    37 Skippers Point Rd, Oakland, MD 21550
  • /56

    $157,000

    Sold Aug 29, 2025

    416 Shenandoah Ave, Oakland, MD 21550

    • 3 Beds
    • 1.5 Baths
    • 975 Sq Ft
    • Built 1940

    Last Sold Summary

    • $161/SF
    • 4 Days On Market

    Current Estimated Value $161,213

    Last Listing Agent Rich Orr Railey Realty, Inc.

    416 Shenandoah Ave, Oakland, MD 21550
    • /95

      Est $528,610

      Not Listed For Sale

      204 Farm View Ln, Oakland, MD 21550

      • 3 Beds
      • 4 Baths
      • 2,268 Sq Ft
      • Built 2007
      204 Farm View Ln, Oakland, MD 21550

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Susan Bell Railey Realty, Inc.

  • /32

    $249,900

    • 2 Beds
    • 1 Bath
    • 772 Sq Ft

    565 Glendale Rd Unit 306, Oakland, MD 21550

    Experience the best of Deep Creek Lake living from this beautifully appointed studio loft at Silver Tree Suites—one of the lake’s most sought-after locations! Offering two separate sleeping areas, a kitchenette, gas fireplace, and private balcony, this unit is designed for comfort and easy getaway living. Tastefully updated with new carpet and flooring, as well as kitchen and bathroom

    Jon Bell Railey Realty, Inc.

    565 Glendale Rd Unit 306, Oakland, MD 21550
  • /39

    $1,065,000

    Sold Jun 18, 2026

    588 Lake Forest Dr, Oakland, MD 21550

    • 3 Beds
    • 2 Baths
    • 1,411 Sq Ft
    • Built 1956

    Last Sold Summary

    • 2% Below List Price
    • $755/SF
    • 6 Days On Market

    Current Estimated Value $1,099,140

    Last Listing Agent Nina Beitzel Railey Realty, Inc.

    588 Lake Forest Dr, Oakland, MD 21550
    • /132

      Est $3,496,418

      Not Listed For Sale

      2524 Stockslager Rd, Oakland, MD 21550

      • 5 Beds
      • 7 Baths
      • 9,134 Sq Ft
      • Built 2006
      2524 Stockslager Rd, Oakland, MD 21550

      Last Sold Summary

      • 15 Days On Market

      Last Listing Agent Melissa Goodfellow Railey Realty, Inc.

  • /64

    $375,000

    $40K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,234 Sq Ft

    1499 Foster Rd, Oakland, MD 21550

    Welcome to Ricky's Retreat, a beautifully renovated mountain retreat nestled on 1.17 private wooded acres in the heart of Garrett County. Ideally located just minutes from Deep Creek Lake, Wisp Resort, Swallow Falls State Park, and downtown Oakland, this turnkey property offers the perfect balance of privacy, recreation, and modern comfort. Originally built as a raised ranch, the home has

    Kelsey Meyers Railey Realty, Inc.

    1499 Foster Rd, Oakland, MD 21550
  • /51

    $425,000

    Sold Oct 22, 2025

    12 Roman Ridge Rd Unit 22B, Oakland, MD 21550

    • 3 Beds
    • 3.5 Baths
    • 2,202 Sq Ft
    • Built 2012

    Last Sold Summary

    • $193/SF
    • 130 Days On Market

    Current Estimated Value $439,576

    Last Listing Agent Andrew Eiswert Railey Realty, Inc.

    12 Roman Ridge Rd Unit 22B, Oakland, MD 21550
    • /42

      Est $462,802

      Not Listed For Sale

      426 Pergin Farm Rd, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 1,596 Sq Ft
      • Built 1985
      426 Pergin Farm Rd, Oakland, MD 21550

      Last Sold Summary

      • 15 Days On Market

      Last Listing Agent Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

  • /48

    $365,000

    $35K PRICE DROP
    • 5 Beds
    • 2 Baths
    • 3,660 Sq Ft

    321 N 3rd St, Oakland, MD 21550

    Reduced and Ready to go!! Perfect one level retirement retreat or 2nd vacation home! Spacious and beautifully maintained all-brick rancher offering approximately 3,660 square feet of living space with room for everyone! This impressive home features 5 bedrooms, 2 full bathrooms, and a fully finished basement with its own private entrance—perfect for in-law potential, extended family living, or

    Christina Ford CENTURY 21 New Millennium

    321 N 3rd St, Oakland, MD 21550
  • /17

    $118,800

    Sold Jun 16, 2026

    1995 Bethlehem Rd, Oakland, MD 21550

    • Land
    • 7.33 Acres
    • $16,207 per Acre

    Last Sold Summary

    • 6 Days On Market

    Last Listing Agent Lana Roby The KW Collective

    1995 Bethlehem Rd, Oakland, MD 21550
    • /81

      Est $683,504

      Not Listed For Sale

      43 Robinwood Dr, Oakland, MD 21550

      • 3 Beds
      • 3.5 Baths
      • 2,921 Sq Ft
      • Built 2005
      43 Robinwood Dr, Oakland, MD 21550

      Last Sold Summary

      • 148 Days On Market

      Last Listing Agent Brian Homberg Taylor-Made Deep Creek Real Estate, LLC

  • /43

    $259,900

    • 3 Beds
    • 2 Baths
    • 1,998 Sq Ft

    102 N 3rd St, Oakland, MD 21550

    Very well maintained 3Br-2BA traditional style home in Oakland with huge 24X24 deck, paved driveway and one car detached garage. Home features almost 2000 square feet of living area, stainless steel appliances, and updated bathrooms. Great place to watch the Autumn Glory parade from you covered front porch. Hot water radiant heat with natural gas being the heat source. Newer replacement windows,

    Kevin Liller Railey Realty, Inc.

    102 N 3rd St, Oakland, MD 21550
  • /20

    $150,000

    Sold Jul 01, 2026

    3395 Fingerboard Rd, Oakland, MD 21550

    • 4 Beds
    • 2 Baths
    • Built 2025

    Last Sold Summary

    • 25% Below List Price
    • 146 Days On Market

    Last Listing Agent Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    3395 Fingerboard Rd, Oakland, MD 21550
    • /44

      Est $683,490

      Not Listed For Sale

      870 Hunters Ridge Dr, Oakland, MD 21550

      • 4 Beds
      • 2.5 Baths
      • 2,896 Sq Ft
      • Built 2007
      870 Hunters Ridge Dr, Oakland, MD 21550

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Mike Kennedy Railey Realty, Inc.

  • /58

    $459,900

    Pending
    • 3 Beds
    • 2 Baths
    • 1,458 Sq Ft

    718 Boy Scout Crosscut Rd, Oakland, MD 21550

    Assumable 2.75% VA loan may be available...contact listing agent for details. If peace and privacy are on your must-have list, this one delivers! Picture this: you pull into the driveway and the trees close in around you on three sides, like the forest itself is standing guard. Over an acre of land, and somehow it stays flat and usable instead of the steep terrain so common in this area. This is

    Jeremy Cunningham Railey Realty, Inc.

    718 Boy Scout Crosscut Rd, Oakland, MD 21550
  • /10

    $55,000

    Sold May 25, 2026

    114 C St, Oakland, MD 21550

    • 768 Sq Ft
    • Built 1999

    Last Sold Summary

    • 8% Below List Price
    • $72/SF
    • 60 Days On Market

    Current Estimated Value $55,500

    Last Listing Agent Jay Ferguson Taylor-Made Deep Creek Real Estate, LLC

    114 C St, Oakland, MD 21550
    • /81

      Est $792,221

      Not Listed For Sale

      335 Mountainview Dr, Oakland, MD 21550

      • 5 Beds
      • 3.5 Baths
      • 3,142 Sq Ft
      • Built 2001
      335 Mountainview Dr, Oakland, MD 21550

      Last Sold Summary

      • 29 Days On Market

      Last Listing Agent Larry Smith Railey Realty, Inc.

  • /115

    $2,350,000

    • 5 Beds
    • 6.5 Baths
    • 5,376 Sq Ft

    2725 Stockslager Rd, Oakland, MD 21550

    Welcome to 2725 Stockslager Road, one of Deep Creek Lake's most coveted properties. This custom-built log home is set against a picturesque landscape in Western Maryland, offering breathtaking nature views and embodying mountain charm and adventure. This home showcases impeccable craftsmanship, seamlessly blending with its natural surroundings while providing unrivaled comfort. Nestled on 1.03

    Shelia McCracken Taylor-Made Deep Creek Real Estate, LLC

    2725 Stockslager Rd, Oakland, MD 21550
  • /37

    $365,900

    Sold Mar 23, 2026

    17979 Garrett Hwy, Oakland, MD 21550

    • 2 Beds
    • 1.5 Baths
    • 960 Sq Ft
    • Built 2005

    Last Sold Summary

    • 2% Above List Price
    • $381/SF
    • 9 Days On Market

    Current Estimated Value $378,673

    Last Listing Agent Dale Carpenter Railey Realty, Inc.

    17979 Garrett Hwy, Oakland, MD 21550
    • /56

      Est $526,526

      Not Listed For Sale

      741 Hoyes Run Rd, Oakland, MD 21550

      • 3 Beds
      • 2 Baths
      • 2,160 Sq Ft
      • Built 1984
      741 Hoyes Run Rd, Oakland, MD 21550

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent Betsy Spiker Holcomb Taylor-Made Deep Creek Real Estate, LLC

  • /72

    $325,000

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,978 Sq Ft

    520 Palmer Ln, Oakland, MD 21550

    Distinguished English Tudor Home in a Private Setting.Nestled on a quiet street with Town of Oakland services, this distinguished English Tudor home offers the perfect blend of privacy, charm, and convenience. Designed with family living in mind, the home features three (3) bedrooms, two (2) full bathrooms, and multiple bonus rooms that provide endless possibilities for a home office,

    Rich Orr Railey Realty, Inc.

    520 Palmer Ln, Oakland, MD 21550
  • /86

    $1,100,000

    Sold Aug 27, 2025

    216 Tarn Dr, Oakland, MD 21550

    • 6 Beds
    • 4.5 Baths
    • 4,769 Sq Ft
    • Built 2020

    Last Sold Summary

    • $231/SF
    • 122 Days On Market

    Current Estimated Value $1,219,101

    Last Listing Agent Betsy Spiker Holcomb Taylor-Made Deep Creek Real Estate, LLC

    216 Tarn Dr, Oakland, MD 21550
    • /71

      Est $927,221

      Not Listed For Sale

      145 Lower Penn Point Dr, Oakland, MD 21550

      • 3 Beds
      • 3.5 Baths
      • 2,106 Sq Ft
      • Built 2007
      145 Lower Penn Point Dr, Oakland, MD 21550

      Last Sold Summary

      • 135 Days On Market

      Last Listing Agent Emillie Albrecht Real Broker, LLC

  • /61

    $444,700

    • 4 Beds
    • 3.5 Baths
    • 1,585 Sq Ft

    333 Sloan Tract Rd, Oakland, MD 21550

    Welcome to *HIDDEN TREASURES*, a beautifully appointed 4-bedroom, 3½-bath home offering the perfect Deep Creek Lake getaway! This established rental property is ideally located close to the lake’s many amenities, making it an excellent opportunity for both personal enjoyment and investment potential. Relax and unwind in the private hot tub after a day of boating, hiking, skiing, or exploring all

    Debra Beitzel Long & Foster Real Estate, Inc.

    333 Sloan Tract Rd, Oakland, MD 21550

Showing Results 361 - 400, Page 10 of 18

How to Buy a Home How to Finance a Home How to Sell a Home